Monoazo dyestuff produced from aminobenzyl-omega-sulfonic acid and acid substituted aromatic amines



til

Patented Apr. 22, 1930 UNITED STATES PATENT OFFICE,

WALTER DUISBERG. OF LEVERKUSEN, AND WINFRID HENTRICH AND LUDWIG ZEH, OF W'IESDORF, HEAR COLOGNE, GERMANY, ASSIGNORS TO GENERAL ANILINE Y WORKS, INC., OF NEW YORK, N. Y., A CORPORATION OF DELAWARE MONOAZO DYESTUFF PRODUCED FROM AMINOBENZYL-w-SULFONIC I SUBSTITUTED AROMATIC No. Drawing. Original application filed February 12, 1926, Serial No. 87,959, and in Germany February ACID AND 4cm 19, 1925. Divided and this application filed February 12, 1926. Serial No. 87,958.

The present invention relates to the new azo dyestuffs of the general formula:

wherein R represents a nucleus of the group including the benzene and naphthalene series: X represents hydrogen, alkyl, aryl or aralkyl, Y represents a sulfonic acid, car;

boxylic acid or hydroxyl group, and Z represents hydrogen or a nitro group. Thedyestufi's are obtained by diazotizing a compound of the general formula:

CH SO H NH: Nor-G2 'wherein Z stands for hydrogen or a nitro group, and coupling the diazo compound thus wherein R repre ents a nucleus of the group including the benzene and naphthalene series and X represents hydrogen, alkyl, aryl or aralkyl and Y represents a sultonic acid, car

hoxylic acid or hydroxyl group. The dyestuffs of this series are .very useful and are especially adapted for dyeing wool.

If the diazo compounds-of nitrated aminobenzyl-w-sulfonic acids are coupled with sul- This classof dyestuffs is illustrated by the following examples:

Emample 1 y 249 parts by weight of the ammonium salt 0f '5-1lltI'O-2-3II1lIi0b8I1ZYl-w-S11lfOI1iC acid are diazotized in an aqueous solution with 69 parts by weight of sodium nitrite and hydrochloric acid. The diazo solution is added to an aqueous solution of 237 parts by weight of Q-methylaminonaphthalene-7-sulfonic acid.

After the coupling is complete the dyestufl is washed with a weakly alkaline solution. It is obtained in a beautifully crystalline form. It dyes wool from an acid bath very clear, uniform, reddish-violet shades which are very, fast to light. The dyestuft', in the form of its sodium salt, has most probably the structural formula HN-OH:

some Ewam'ple 2 277 parts by weight of 3.5-dinitro-2-aminobenzyl-o-sulfonic acid are diazotized and the I 277 parts by weight of 3.5-dinitro-2-aminobenzylam-sulfomc acid are diazotized. The i diazo compound is added to an aqueuossolution of 209 parts by weight of the sodium salt of 2-naphthylamine-3-carboxylic acid.

The dyestufi' is worked up in the usual manner. It dyes wool clear, level, reddish-violet shades of good fastness to light and fulling. The sodium salt of the dyestuii has most probably the structural formula:

4 NH: GOONa HzC-SOaNa OzN N0:

NH: mo-soma no- OzN NOz Example 5 294: parts by weight of the ammonium salt of 3.5 dinitro4-aminobenzyl-w-sulfonic acid are diazotized. The diazo compound is added to an aqueous solution of 251 parts by weight of Q-ethylaminonaphthalene-7-sulfonic acid. The dyestuff is worked up in the usual manner. It dyes Wool level Bordeaux shades of excellent fastness to light and fulling. The ammonium salt of'the dyestufi has most probably the structural formula:

Additional examples are "given in the following table:

Diazo compound from-- Shades of the dye- Couplcd \v1th- Sums v 5-nitro-2-aminobenzyl-w-su1fonic acid 2-methylamine-S-naphthol-Gsulfonic acid Bluish-violet. 3.5-dinitro-2-aminobenzyl-w-sulfonic acid 2-methylaminonaphthalenc-7-sulfonic acid .1 Clear bluish-violet. 3.5-dinitro2-amlnobenzyl-w-sulfonic ucid 2-naphthylamine-6-sulfonic acid Bordeaux. 3.5-dinitro-2'aminobenzylw-su1fonic acid--- Phenyl-2-naphthylamine-G-sulfonic acid a. Violet.

The dyestufi, in the form of its sodium salt, has most probably the structural formula:

HaC-SOaNa 1 N01 OzN dinitlo-2-uminobenzyl-w-sulfonic acid 2-amlno-8-naphthol-6-sulfonic acid Reddlsh-blue. dinitro-2amlnobenzyl-w-su1fonic acid 2-phenylamino8-naphthol-6-sulfonic acid Violet-black.

The dyestuff, in the form of its sodium salt, has most probably the structural formula:

Hill-S OaNa olN N02 HN-C Ha SOaNa This application i's'a division of our parent application, Serial No." 87,959.

We claim 1. As new products the compounds of the general formula:

wherein R represents a nucleus of the group including the benzene and naphthalene series and X represents hydrogen, alkyl, aryl or aralkyl, Y represents a sulfonic acid, carboxylic acid or hydroxyl group and Z represents hydrogen or a nitro group.

2. As new products the compounds of the general formula: I

' cmsoan wherein R'represents a nucleus of the group including the benzene and naphthalene seor aralkyl andY represents a sulfonic acid, carboxylic acid or hydroxyl group.

3. As new products the compounds of the general formula:

omsom som wherein R represents a nucleus of the group including the benzene and naphthalene series and X represents hydrogen, alkyl, aryl or aralkyl. v

4. As new products the compounds of the general formula: a

x x emsom N wherein X re resents hydrogen,.alkyl, aryl or aralkyl an Y represents a sulfonic acid, carboxylic acid or hydroxyl group and a represents hydrogen or a mtro group.

5. As new products the compounds of the general formula:

wherein Z stands for hydrogen, a methyl or ethyl group.

6. As a new product the compound of the probable formula:

10. As new products wool material dyed with the monoazo dyestufl'sdefined in claim 4. 11. As new products wool material dyed with the monoazo dyestuffs defined in claim 5. 12. As a new product-wool material dyed with diazo dyestuff defined in claim 6.

In testimony whereof we have hereunto set WALTER DUISBERG. WINFRID HENTRICH. LUDWIG ZEH.

our hands.

ries and X represents hydrogen, alkyl, aryl 

